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Merck
CN

H0513

Heptakis(2,6-di-O-methyl)-β-cyclodextrin

Synonym(s):

DM-β-CD, DM‐β‐CyD, heptakis-(2,6-O-Dimethyl)-β-cyclodextrin, 2,6-Di-O-methyl-β-cyclodextrin, Dimethyl β-cyclodextrin

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About This Item

Empirical Formula (Hill Notation):
C56H98O35
CAS Number:
51166-71-3
Molecular Weight:
1331.36
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24895404
MDL number:
MFCD00011616
Beilstein/REAXYS Number:
1679144

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InChI

1S/C56H98O35/c1-64-15-22-36-29(57)43(71-8)50(78-22)86-37-23(16-65-2)80-52(45(73-10)30(37)58)88-39-25(18-67-4)82-54(47(75-12)32(39)60)90-41-27(20-69-6)84-56(49(77-14)34(41)62)91-42-28(21-70-7)83-55(48(76-13)35(42)63)89-40-26(19-68-5)81-53(46(74-11)33(40)61)87-38-24(17-66-3)79-51(85-36)44(72-9)31(38)59/h22-63H,15-21H2,1-14H3/t22-,23-,24-,25-,26-,27-,28-,29+,30+,31+,32+,33+,34+,35+,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-/m1/s1

SMILES string

COC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](OC)[C@H](O[C@@H]3COC)O[C@H]4[C@H](O)[C@@H](OC)[C@H](O[C@@H]4COC)O[C@H]5[C@H](O)[C@@H](OC)[C@H](O[C@@H]5COC)O[C@H]6[C@H](O)[C@@H](OC)[C@H](O[C@@H]6COC)O[C@H]7[C@H](O)[C@@H](OC)[C@H](O[C@@H]7COC)O[C@H]8[C@H](O)[C@@H](OC)[C@H](O[C@@H]8COC)O[C@H]1[C@H](O)[C@H]2OC

InChI key

QGKBSGBYSPTPKJ-UZMKXNTCSA-N

biological source

synthetic

form

powder

Quality Level

200

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General description

Heptakis(2,6-di-O-methyl)-β-cyclodextrin is a hydrophilic derivative of cyclodextrin that possesses the ability to effectively dissolve lipophilic drugs like steroid hormones, vitamins A, E, and K, etc. It can be utilized to increase the dissolution and bioavailability of weakly water-soluble pharmaceutical compounds.

Application

Heptakis(2,6-di-O-methyl)-β-cyclodextrin may be used:
  • To measure the equilibrium constant of its complexes with various enantiomeric pairs of chiral nitroxides by electron paramagnetic resonance (EPR) spectroscopy.
  • To study the crystal structure of its complex with n-butyl acrylate and isobornyl acrylate using X-ray diffraction (XRD).
  • As a chiral selector to resolve amphetamine related drugs by capillary zone electrophoresis.

Reactant involved in:
  • Physicochemical studies of inclusion complexes
  • Probing diffusion and single molecule interactions with reconstituted membrane proteins
  • Interactions with micelles causing micellar rupture
  • Studying cellular transport, used as a cell penetration enhancer
  • Physicochemical and biopharmaceutical improvement of drugs particularly with solubilization and stability
  • Interactions with cholesterol

Analysis Note

Impurities are over-methylated homologs, primarily hexakis(2,6-di-O-methyl)-(2,3,6-tri-O-methyl)-β-cyclodextrin.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCD6677
SLBW0877
SLCB9691
SLBT7645
SLCB3078

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Z Aigner et al.
Journal of pharmaceutical and biomedical analysis, 57, 62-67 (2011-09-17)
The steps of formation of an inclusion complex produced by the co-grinding of gemfibrozil and dimethyl-β-cyclodextrin were investigated by differential scanning calorimetry (DSC), X-ray powder diffractometry (XRPD) and Fourier transform infrared (FTIR) spectroscopy with curve-fitting analysis. The endothermic peak at
F Hirayama et al.
Journal of pharmaceutical sciences, 88(10), 970-975 (1999-10-09)
Acetyl groups were introduced to the hydroxyl groups of heptakis(2, 6-di-O-methyl)-beta-cyclodextrin (DM-beta-CyD), and the resulting heptakis(2,6-di-O-methyl-3-O-acetyl)-beta-CyD (DMA-beta-CyD) was evaluated for the inclusion property and hemolytic activity. It was confirmed by means of NMR and mass spectroscopies that in the DMA-beta-CyD
Shaimaa M Badr-Eldin et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 70(3), 819-827 (2008-07-29)
The aim of this work was to investigate the inclusion complexation between tadalafil, a practically insoluble selective phosphodiesterase-5 inhibitor (PDE5), and two chemically modified beta-cyclodextrins: hydroxypropyl-beta-cyclodextrin (HP-beta-CD) and heptakis-[2,6-di-O-methyl]-beta-cyclodextrin (DM-beta-CD), in comparison with the natural beta-cyclodextrin (beta-CD) in order to
Kanokthip Boonyarattanakalin et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 47(4), 752-758 (2012-08-28)
The inclusion complexes of highly potent anti-HIV agent, UC781, with β-cyclodextrin (βCD), 2,6-dimethyl-β-cyclodextrin (MβCD), and 2-hydroxypropyl-β-cyclodextrin (HPβCD) in aqueous solution were investigated by molecular dynamics simulations. Simulations show that the phenyl ring of UC781 is trapped inside CD cavities, while
Michelle Amoako-Tuffour et al.
Acta pharmaceutica (Zagreb, Croatia), 59(4), 395-405 (2009-11-19)
The potential for nasal delivery of losartan, a drug with poor oral bioavailability, was investigated using Calu-3 cells. Epithelial permeation of the drug with or without dimethyl-beta-cyclodextrin (DM-beta-CD) and glycocholate was investigated. Possible transport mechanism of the compound and epithelial
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